Emulsions comprising essential oil components

Abstract

This invention discloses an emulsion comprising one or more essential oil components and one or more monoglycerides. An exemplary embodiment includes an aqueous medium, a first phase dispersed in the aqueous medium, and a second phase dispersed in the aqueous medium. The first phase comprises one or more essential oil components, and the second phase comprises C4–C... 28 One or more monoglycerides of fatty acids.

Description

[0001] Cross-reference to related applications

[0002] This application claims priority to U.S. Provisional Application No. 63 / 544015, filed on October 13, 2023, the contents of which are incorporated herein by reference in their entirety. Technical Field

[0003] The disclosure in this application pertains to coatings used in agricultural products. Background Technology

[0004] Common agricultural products are readily degraded and decomposed (i.e., spoiled) when exposed to the environment. Such agricultural products can include, for example, eggs, fruits, vegetables, agricultural products, seeds, nuts, flowers, and / or whole plants (including their processed and semi-processed forms). Non-agricultural products (e.g., vitamins, confectionery, etc.) are also readily degraded when exposed to the surrounding environment. Degradation of agricultural products can occur via abiotic mechanisms due to moisture loss through evaporation from the outer surface of the product to the atmosphere and / or oxidation caused by oxygen diffusing from the environment into the product and / or mechanical damage to the surface and / or photoinduced degradation (i.e., photodegradation). Furthermore, biological stressors such as bacteria, fungi, viruses, and / or pests can also infect and decompose agricultural products.

[0005] Conventional methods for preventing degradation, maintaining quality, and extending the shelf life of produce include refrigeration and / or specialized packaging. Refrigeration requires capital-intensive equipment, constant energy consumption, and can damage or degrade the product if not carefully controlled; it must be actively managed, and its benefits are lost when the temperature-controlled supply chain is disrupted. Specialized packaging also requires expensive equipment, consumes packaging materials, increases transportation costs, and requires active management. While refrigeration and specialized packaging can provide benefits, the handling and transportation of produce can cause surface abrasions or scratches, which are aesthetically unpleasant for consumers and can serve as entry points for bacteria and fungi. Furthermore, the costs associated with such methods increase the overall cost of produce. Summary of the Invention

[0006] This application provides an emulsion comprising an aqueous medium, a first phase dispersed in the aqueous medium, and a second phase dispersed in the aqueous medium. The first phase comprises one or more essential oil components, present in a total amount of about 0.001% to about 10% by weight of the emulsion, and the second phase comprises C4-C4 components. 28 One or more glycerol monoesters of fatty acids, present in a total amount of about 0.1% to about 30% by weight of the emulsion.

[0007] This application also provides a method for preparing an emulsion. The method includes combining a first mixture at a first temperature and a second mixture at a second temperature to produce a third mixture, and agitating the third mixture to produce an emulsion. The first mixture comprises one or more essential oil components and a surfactant, and the second mixture comprises an aqueous medium and C4-C... 28 One or more monoglycerides of fatty acids. The emulsion comprises a first phase dispersed in the aqueous medium and a second phase dispersed in the aqueous medium, the first phase comprising the one or more essential oil components and the second phase comprising the one or more monoglycerides.

[0008] This application also provides emulsions prepared according to the method of this application.

[0009] This application also provides a method for coating agricultural products, the method comprising bringing the surface of the agricultural product into contact with the emulsion of this application, and removing at least a portion of an aqueous medium to form a coating on the surface of the agricultural product.

[0010] This application also provides a method for coating agricultural products, the method comprising contacting the surface of the agricultural product with a first emulsion and a second emulsion. The first emulsion comprises a first aqueous medium and a first phase dispersed in the first aqueous medium, the first phase comprising one or more essential oil components, and the second emulsion comprises a second aqueous medium and a second phase dispersed in the second aqueous medium, the second phase comprising C4-C... 28 One or more monoglycerides of fatty acids.

[0011] The accompanying drawings and description illustrate details of one or more embodiments of the subject matter of this application. Other features, aspects, and advantages of the subject matter will become apparent from the description, claims, and drawings. Invention Details

[0013] This application discloses emulsions comprising one or more essential oil components and one or more monoglycerides. Specifically, the emulsions of this application may include a first phase and a second phase, each dispersed in an aqueous medium, the first phase comprising one or more essential oil components and the second phase comprising one or more monoglycerides. Such emulsions can remain stable over extended periods and can be applied to agricultural products to provide coatings with antifungal and gas- and / or water-resistant properties. Furthermore, the emulsions may have limited phytotoxicity while providing improved overall traceability.

[0014] Specific embodiments of the disclosed subject matter will now be described in detail. While the disclosed subject matter will be described in conjunction with the enumerated claims, it should be understood that the exemplary subject matter is not intended to limit the claims to the disclosed subject matter.

[0015] definition

[0016] The terms "a," "an," and "the" are used in this application to include one or more, unless the context clearly specifies otherwise. Unless otherwise stated, the term "or" is used to refer to a non-exclusive "or." The expression "at least one of A and B" has the same meaning as "A, B, or A and B." Furthermore, it should be understood that any use of expressions or terms in the disclosure of this application, unless otherwise stated, is intended to aid in reading the document and should not be construed as restrictive; information relating to a section heading may occur within or outside that particular section.

[0017] Numerical values ​​expressed in range format should be interpreted flexibly to include not only the values ​​explicitly listed as range limits, but also all individual values ​​or subranges contained within that range, as if each value and subrange were explicitly stated. For example, the range "about 0.1% to about 5%" or "about 0.1% to 5%" should be interpreted to include not only about 0.1% to about 5%, but also the individual values ​​(e.g., 1%, 2%, 3%, and 4%) and subranges (e.g., 0.1% to 0.5%, 1.1% to 2.2%, 3.3% to 4.4%) within the indicated range. Unless otherwise stated, the statement "about X to Y" has the same meaning as "about X to about Y". Similarly, the statement "about X, Y, or about Z" has the same meaning as "about X, about Y, or about Z", unless otherwise stated.

[0018] As used in this application, the term "about" allows for a degree of variability within 10% of the said numerical value or range limit.

[0019] In the method of this application, actions can be performed in any order, except when a time or sequence of operations is explicitly listed. Furthermore, unless the explicit language of the claims specifies that they are performed separately, the specified actions can be performed simultaneously. For example, the claimed action X and the claimed action Y can be performed simultaneously within a single operation, and the resulting process will fall within the literal scope of the claimed process.

[0020] As used herein, the term "monoglyceride" refers to the condensation product of a glycerol molecule and a fatty acid—that is, a glycerol group attached to a fatty acid via an ester bond. Monoglycerides can, but do not necessarily, originate from a condensation reaction. For example, monoglycerides can be obtained through esterification between glycerol and a fatty acid, or through transesterification (glycerolysis) of a triglyceride with glycerol. Monoglycerides can also be called monoalkyl glycerides. When the glycerol group is attached to an ester bond at the 1-position (e.g., as in 2,3-dihydroxypropyl-1-yloctadecanoate), the monoglyceride can be called a 1-monoglyceride or a 1-alkyl glyceride (e.g., as in 1-octadecanoate). When the glycerol group is attached to an ester bond at the 2-position (e.g., as in 1,3-dihydroxypropyl-2-ylhexadecanoate), the monoglyceride can be called a 2-monoglyceride or a 2-alkyl glyceride (e.g., as in 2-hexadecanoate). The glycerol group of the monoglyceride may be unsubstituted (e.g., as in 2,3-dihydroxypropyl-1-ylalkyl ester), or may be further substituted with one or more groups other than fatty acids (e.g., as in 1,3-dialkoxypropyl-2-ylalkyl ester).

[0021] As used in this application, the term "fatty acid" refers to a carboxylic acid having an aliphatic side chain. Fatty acids may be naturally occurring or non-naturally occurring and may include branched or unbranched (e.g., linear), substituted or unsubstituted, and saturated or unsaturated side chains.

[0022] As used in this application, the term "side chain" refers to the aliphatic portion or a portion thereof of a fatty acid. Unless otherwise stated, the side chain of a given fatty acid includes the carbon atom of a carboxylic acid group. For example, dodecanoic acid can be described as including a linear, saturated C14-carbon group. 12 Side chain, also represented as R H -C(O)OH, where R H It is linear, saturated C. 11 Side chains. Side chains can exist in compounds other than fatty acids, such as esters or amides, and can, but do not have to, be derived from fatty acids. For example, dodecanoic acid amide can be described as an amide of a fatty acid, regardless of whether the compound is actually derived from dodecanoic acid.

[0023] The term "salt" as used with respect to the disclosed compounds (e.g., fatty acids) refers to a derivative of the compound in which the parent compound is modified by converting the acid or base portion into its salt form. Examples of such salts include, but are not limited to, inorganic or organic acid salts of basic residues such as amines, and basic or organic salts of acidic residues such as carboxylic acids.

[0024] Where certain features of the compounds disclosed in this application are disclosed by group or range, such disclosure includes each individual sub-combination of members of such group and range. For example, the term "C1-C6 alkyl" includes (but is not limited to) methyl, ethyl, C3 alkyl, C4 alkyl, C5 alkyl, and C6 alkyl.

[0025] As used in this application, the term "n-membered" (where n is an integer) generally describes the number of ring-forming atoms in a portion of which the number of ring-forming atoms is n. For example, piperidinyl is an example of a 6-membered heterocyclic alkyl ring, and 1,2,3,4-tetrahydro-naphthalene is an example of a 10-membered cycloalkyl ring.

[0026] As used in this application, the term "substituted" means an atom or atomic group that formally replaces hydrogen as a "substituent" attached to another group. Unless otherwise stated, "substituted" means any level of substitution, such as mono-, di-, tri-, tetra-, or penta-substituted, where such substitution is permitted. Substituents are chosen independently, and substitution can be at any chemically realizable position. Substitution at a given atom is limited by valence. The phrase "optionally substituted" means unsubstituted or substituted. A single divalent substituent, such as an oxo, can substitute for two hydrogen atoms.

[0027] As used in this application, the term "C" n -C m The indication includes the range of endpoints, where n and m are integers and indicate the number of carbons. Examples include C1-C4, C1-C6, etc.

[0028] As used in this application, the term "alkyl" refers to a saturated hydrocarbon group that can be straight-chain or branched. The term "C"... n -C m "Alkyl" refers to an alkyl group having n to m carbon atoms. An alkyl group formally corresponds to an alkane in which a CH bond is replaced by the alkyl group at the junction with the rest of the compound. Examples of alkyl moieties include, but are not limited to, chemical groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl; and higher homologues such as 2-methyl-1-butyl, n-pentyl, 3-pentyl, n-hexyl, 1,2,2-trimethylpropyl, etc.

[0029] As used herein, the term "alkenyl" refers to a straight-chain or branched hydrocarbon group corresponding to an alkyl group having one or more carbon-carbon double bonds. An alkenyl group formally corresponds to an alkene in which a CH bond is replaced by a connection point between the alkenyl group and the remainder of the compound. The term "C..." n -C m "Alkenyl" refers to an alkenyl group having n to m carbon atoms. Examples of alkenyl groups include, but are not limited to, vinyl, n-propenyl, isopropenyl, n-butenyl, sec-butenyl, etc.

[0030] As used in this application, the term "alkoxy" refers to a group of the formula -O-alkyl, wherein the alkyl group is as defined above. The term "C"... n -C m "Alkoxy" refers to an alkoxy group whose alkyl group has n to m carbons. Examples of alkoxy groups include methoxy, ethoxy, propoxy (i.e., n-propoxy and isopropoxy), tert-butoxy, etc.

[0031] As used in this application, the term "cycloalkyl" refers to a non-aromatic hydrocarbon ring system (monocyclic, bicyclic, or polycyclic), including cycloalkyl and alkenyl groups. The term "C"... n -C m "Cycloalkyl" refers to a cycloalkyl group having n to m ring member carbon atoms. Cycloalkyl groups can include fused, bridged, and / or spirobicyclic or polycyclic systems. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cyclohexadienyl, cyclohepttrienyl, norbornyl, norpinel, norcarel, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.2.0]hexyl, bicyclo[3.1.0]hexyl, bicyclo[3.2.0]heptyl and bicyclo[3.3.0]octyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl and bicyclo[1.1.1]pentyl, etc.

[0032] As used herein, the term "heterocyclic alkyl" refers to a non-aromatic ring system (monocyclic, bicyclic, or polycyclic) that optionally contains one or more alkenyl groups as part of a ring structure and has at least one heteroatom ring member independently selected from nitrogen, sulfur, oxygen, and phosphorus. The term "n- to m-membered ring heterocyclic alkyl" refers to a heterocyclic alkyl group having n to m cyclic atoms. The cyclic carbon atoms and heteroatoms of the heterocyclic alkyl group may optionally be oxidized to form oxo or thio groups or other oxidized bonds (e.g., C(O), S(O), C(S), S(O)2). N(e.g., -O group) or nitrogen atoms can be quaternized. Heterocyclic alkyl groups can be linked by cyclic carbon atoms or cyclic heteroatoms. Heterocyclic alkyl groups can include double bonds, for example, up to three double bonds. Examples of heterocyclic alkyl groups include, but are not limited to, aza-butane, dihydrofuranyl, dihydrothiopheneyl, tetrahydrothiopheneyl, tetrahydrofuranyl, tetrahydrotriazinyl, tetrahydropyrazolyl, tetrahydrooxazinyl, tetrahydropyrimidinyl, octahydrobenzofuranyl, octahydrobenzimidazolyl, octahydrobenzothiazolyl, imidazolyl, pyrrolidinyl, piperidinyl, piperazinyl, oxazolyl, thiazolyl, pyrazolyl, thiomorpholinyl, tetrahydropyranyl, tetrahydrothiazolyl, tetrahydrothiadiazinyl, tetrahydrooxazolyl, morpholinyl, oxacyclobutane, dioxacyclobutane, dioxalyl, oxacycloheptane, dioxane The group includes alkyl, oxazinyl, dioxazinyl, tetrahydrodiazinyl, oxazinyl, oxazinyl, quininyl, chromanyl, isochrysanyl, dihydrobenzodioxinyl, benzodioxazinyl, benzodioxane, indolinyl, dihydrobenzofuranyl, tetrahydroquinolinyl, isochrysanyl, dihydro-1H-isoindolyl, 2-azabicyclo[2.2.1]heptanone, 3-azabicyclo[3.1.0]hexyl, 3-azabicyclo[4.1.0]heptyl, etc. Other examples of heterocyclic alkyl groups include tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, imidazolidine-1-yl, imidazolidine-2-yl, imidazolidine-4-yl, pyrrolidine-1-yl, pyrrolidine-2-yl, pyrrolidine-3-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, piperazine-1-yl, piperazine-2-yl, 1,3-oxazolidine-3-yl, 1,4- Oxazolidinyl heptane-1-yl, isothiazolyl, 1,3-thiazolidinyl-3-yl, 1,2-pyrazolyl-2-yl, 1,2-tetrahydrothiazinyl-2-yl, 1,3-thiazinyl-3-yl, 1,2-tetrahydrodiazinyl-2-yl, 1,3-tetrahydrodiazinyl-1-yl, 1,4-oxazinyl-4-yl, oxazolidinoneyl, 2-oxo-piperidinyl (e.g., 2-oxo-piperidinyl-1-yl), etc.

[0033] As used in this application, the term "essential oil" refers to an oil derived from herbs or other plants, for example, through distillation, pressing, solvent extraction, and cold pressing. Essential oils can be extracted from the whole plant or any part thereof, including leaves, flowers, stems, roots, seeds, and combinations thereof. As used in this application, the term "essential oil component" refers to an essential oil or any one or more compounds thereof. Essential oil components may, but are not necessarily, derived from herbs or other plants. For example, an "essential oil component" including lavender oil may refer to lavender oil or one or more compounds thereof, which may be naturally derived or synthetically prepared. In another example, an "essential oil component" including cinnamon oil may refer to cinnamon oil or one or more compounds thereof, such as 2-methoxycinnamaldehyde, trans-cinnamaldehyde, or both, which may be naturally derived or synthetically prepared.

[0034] The term "Crawford temperature" as used herein, in relation to compositions containing monoglycerides, refers to the lowest temperature at which monoglycerides can form vesicles.

[0035] lotion

[0036] This application provides an emulsion comprising an aqueous medium, a first phase dispersed in the aqueous medium, and a second phase dispersed in the aqueous medium. The first phase comprises one or more essential oil components, present in a total amount of about 0.001% to about 10% by weight of the emulsion, and the second phase comprises C4-C 28 One or more glycerol monoesters of fatty acids, present in a total amount of about 0.1% to about 30% by weight of the emulsion.

[0037] In some embodiments, the first phase comprises droplets containing one or more essential oil components. In some embodiments, the first phase comprises droplets with an average diameter of about 10 nm to about 1,000 nm, such as about 10 nm to about 500 nm, about 10 nm to about 300 nm, about 25 nm to about 1,000 nm, about 25 nm to about 500 nm, about 25 nm to about 300 nm, about 50 nm to about 1,000 nm, about 50 nm to about 500 nm, or about 50 nm to about 300 nm. In some embodiments, the first phase comprises droplets having a d90 diameter distribution of up to about 500 nm, such as up to about 450 nm, up to about 400 nm, up to about 350 nm, up to about 300 nm, or up to about 250 nm.

[0038] In some embodiments, the one or more essential oil components include lavender oil, rose oil, ylang-ylang oil, eucalyptus oil, sweet orange oil, chamomile oil, peppermint oil, jasmine oil, lemon oil, lemongrass oil, tea tree oil, frankincense oil, grapefruit oil, clove oil, cinnamon oil, vanilla oil, rosemary oil, white tea oil, bergamot oil, sage oil, laurel oil, geranium oil, patchouli oil, sandalwood oil, immortelle oil, oregano oil, pine needle oil, eucalyptus cone oil, camphor oil, benzoin oil, fennel oil, thyme oil, nutmeg oil, lemon eucalyptus oil, ravensara leaf oil, wild orange oil, myrrh oil, osmanthus oil, cypress oil, artemisia oil, basil oil, vetiver oil, juniper spearmint oil, lemon balm oil, ginger oil, gardenia oil, lotus seed oil, neroli oil, palmarosa oil, mandarin orange oil, and citronella oil. Oils such as litsea cubeba oil, rosewood oil, valerian oil, verbena oil, cypress oil, lime pepper oil, magnolia oil, or any combination thereof. For example, in some embodiments, one or more essential oil components include rosemary oil, ylang-ylang oil, cinnamon bark oil, cinnamon leaf oil, or any combination thereof. In some embodiments, the one or more essential oil components include citral, methyl eugenol, 2-methoxycinnamaldehyde, trans-cinnamaldehyde, trans, trans-2,4-decanoic acid, benzaldehyde, 1,8-cineole, α-pinene, or any combination thereof. In some embodiments, one or more essential oil components include trans-cinnamaldehyde and rosemary oil. In some embodiments, one or more essential oil components include trans-cinnamaldehyde, methyl eugenol, and citral.

[0039] In some embodiments, the total amount of one or more essential oil components present in the emulsion is from 0.001 wt% to about 7.5 wt%, from about 0.001 wt% to about 5 wt%, from about 0.01 wt% to about 10 wt%, from about 0.01 wt% to about 7.5 wt%, from about 0.01 wt% to about 5 wt%, from about 0.1 wt% to about 10 wt%, from about 0.1 wt% to about 7.5 wt%, or from about 0.1 wt% to about 5 wt%. In some embodiments, the first phase comprises at least 50 wt% of the total amount of essential oil components present in the emulsion, such as at least 60 wt%, at least 70 wt%, at least 80 wt%, or at least 90 wt%.

[0040] In some embodiments, the second phase comprises vesicles containing one or more monoglycerides. In some embodiments, the second phase comprises vesicles with an average diameter of about 10 nm to about 1,000 nm, such as about 10 nm to about 500 nm, about 10 nm to about 200 nm, about 50 nm to about 1,000 nm, about 50 nm to about 500 nm, about 50 nm to about 200 nm, about 100 nm to about 1,000 nm, about 100 nm to about 500 nm, or about 100 nm to about 200 nm. In some embodiments, the second phase comprises vesicles with a d90 diameter distribution of up to about 900 nm, such as up to about 800 nm, up to about 700 nm, up to about 600 nm, up to about 500 nm, or up to about 450 nm.

[0041] In some implementations, the second phase includes C4-C 28 A monoglyceride of fatty acids. In some embodiments, the second phase comprises C4-C 28 Two, three, or more monoglycerides of fatty acids, such as C4-C 28 Two types of monoglycerides of fatty acids. In some embodiments, the monoglycerides include one or more monoglycerides of naturally occurring fatty acids.

[0042] The monoglyceride may include one or more 1-monoglycerides, one or more 2-monoglycerides, or mixtures thereof. In some embodiments, the monoglyceride includes 2,3-dihydroxypropyl-1-yl esters of one or more fatty acids, 1,3-dihydroxypropyl-2-yl esters of one or more fatty acids, or mixtures thereof. In some embodiments, the 1-monoglyceride accounts for at least about 50% by weight, at least about 60% by weight, at least about 70% by weight, at least about 75% by weight, at least about 80% by weight, at least about 85% by weight, at least about 90% by weight, or at least about 95% by weight, or about 100% by weight of the monoglycerides present in the emulsion. In some embodiments, the 1-glyceromonoester accounts for about 70% to about 100% by weight, about 70% to about 95% by weight, about 70% to about 90% by weight, about 75% to about 100% by weight, about 75% to about 95% by weight, about 75% to about 90% by weight, about 80% to about 100% by weight, about 80% to about 95% by weight, or about 80% to about 90% by weight of the glyceromonoester present in the emulsion.

[0043] In some implementations, the monoglyceride includes C6-C 28 Fatty acids, C8-C 28 Fatty acids, C4-C 24 Fatty acids, C6-C 24 Fatty acids, C 12 -C 24 Fatty acids, C4-C22 Fatty acids, C6-C 22 Fatty acids or C 12 -C 22 One or more monoglycerides of fatty acids. In some embodiments, the one or more monoglycerides include unsubstituted side chains, such as unsubstituted C... 12 -C 22 Side chain. In some embodiments, one or more glycerol monoesters include a linear side chain, such as a linear C-chain. 12 -C 22 Side chain. In some embodiments, one or more glycerol monoesters include saturated side chains, such as saturated C42-C ... 12 -C 22 Side chain.

[0044] In some embodiments, the glycerol monoester comprises one or more compounds of formula Ii:

[0045] (Formula Ii)

[0046] in:

[0047] R A1 and R A2 Each is independently selected from H and C1-C6 alkyl groups; and

[0048] R H It is C3-C 27 Side chain.

[0049] In some embodiments, the glycerol monoester comprises one or more compounds of formulas I-ii:

[0050] (Formula I-ii)

[0051] in:

[0052] R A1 and R A2 Each is independently selected from H and C1-C6 alkyl groups; and

[0053] R H It is C3-C 27 Side chain.

[0054] In some embodiments, one or more glycerol monoesters each independently comprise a compound of formula Ii or formula I-ii. In some embodiments of formula Ii or formula I-ii, R A1 and R A2 Each is H. In some implementations of formula Ii or formula I-ii, R H It is a saturated side chain. In some embodiments of formula Ii or formula I-ii, R HIt is an unsubstituted side chain. In some embodiments of formula Ii or formula I-ii, R H It is a straight-chain side chain. In some embodiments of formula Ii or formula I-ii, R H It is C5-C 17 Side chain. In some embodiments of formula Ii or formula I-ii, R H It is C 11 -C 21 Side chain.

[0055] In some embodiments, the glycerol monoester comprises a first compound of formula Ii or formula I-ii, wherein R H It is C 15 -C 27 Fatty acid chains; and a second compound of formula Ii or I-ii, wherein R H It is C3-C 13 Fatty acid chain. In some embodiments, the R of the first compound... H It is C 15 -C 21 Fatty acid chain, and R of the second compound. H It is C 11 -C 13 Fatty acid chains.

[0056] In some embodiments, the glycerol monoester comprises one or more compounds of formula IA-i:

[0057] (Formula IA-i)

[0058] in:

[0059] R A1 and R A2 Each is independently selected from H and C1-C6 alkyl groups;

[0060] R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 and R 9 Each is independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy;

[0061] Each occurrence of R 10A R 10B R 11A and R 11B Independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy;

[0062] R on adjacent carbon atoms 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10A R 10B R 11A and R 11B Any two of them can combine with the carbon atoms they are attached to to form a double bond, a 3- to 6-membered heterocyclic alkyl group, or a C3-C6 cycloalkyl group;

[0063] o is an integer between 0 and 17;

[0064] p is an integer between 0 and 17; and

[0065] The sum of o and p is 0-17.

[0066] In some embodiments, the glycerol monoester comprises one or more compounds of formula IA-ii:

[0067] (Formula IA-ii)

[0068] in:

[0069] R A1 and R A2 Each is independently selected from H and C1-C6 alkyl groups;

[0070] R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 and R 9 Each is independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy;

[0071] Each occurrence of R 10A R 10B R 11A and R 11B Independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy;

[0072] R on adjacent carbon atoms 1 R 2 R 3 R 4 R5 R 6 R 7 R 8 R 9 R 10A R 10B R 11A and R 11B Any two of them can combine with the carbon atoms they are attached to to form a double bond, a 3- to 6-membered heterocyclic alkyl group, or a C3-C6 cycloalkyl group;

[0073] o is an integer between 0 and 17;

[0074] p is an integer between 0 and 17; and

[0075] The sum of o and p is 0-17.

[0076] In some embodiments, one or more glycerol monoesters each independently comprise a compound of formula IA-i or formula IA-ii. In some embodiments of formula IA-i or formula IA-ii, R A1 and R A2 Each is H. In some implementations of formula IA-i or formula IA-ii, each R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 and R 9 And each occurrence of R 10A R 10B R 11A and R 11B Independently selected from H and OH. In some embodiments of formula IA-i or IA-ii, R is placed on adjacent carbon atoms. 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10A R 10B R 11A and R 11B Any two of them can combine with the carbon atoms they are attached to to form oxirane. In some embodiments of formula IA-i or IA-ii, R is located on adjacent carbon atoms. 1 R 2 R 3 R 4 R5 R 6 R 7 R 8 R 9 R 10A R 10B R 11A and R 11B Any two pairs, one pair, or no combination thereof, together with the carbon atoms they are attached to form a double bond. In some embodiments of formula IA-i or IA-ii, R on adjacent carbon atoms 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10A R 10B R 11A and R 11B The pair or uncombined forms of R combine with the carbon atoms they are attached to to form ethylene oxide. In some embodiments of formula IA-i or IA-ii, R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 Two, one, or none of them, and R in each occurrence 10A R 10B R 11A and R 11B It is OH.

[0077] In some implementations of formula IA-i or formula IA-ii, the sum of o and p is 0-13, 0-11, 0-9, 0-7, 5-17, 5-13, 5-11, 5-9, 5-7, 7-17, 7-13, 7-11, 7-9, 9-17, 9-13, 9-11, 11-17, or 11-13.

[0078] In some embodiments, the glycerol monoester comprises one or more 1-glycerol monoesters or 2-glycerol monoesters, such as 2,3-dihydroxypropyl-1-yl esters or 1,3-dihydroxypropyl-2-yl esters of the following acids: heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, dodecanoic acid, 9-hydroxyhexadecanoic acid, 10-hydroxyhexadecanoic acid, 9,10-dihydroxyhexadecanoic acid, 16-hydroxyhexadecanoic acid, 9,16-dihydroxyhexadecanoic acid, 10,16-dihydroxyhexadecanoic acid, 9,10,16-trihydroxyhexadecanoic acid, 9,10-epoxyhexadecanoic acid, (9Z)-hexadecano-9-enoic acid, (9E)-hexadecano-9-enoic acid, 9,10- Epoxy-16-hydroxyhexadecanoic acid, 16-hydroxy-(9Z)-hexadec-9-enoic acid, 16-hydroxy-(9E)-hexadec-9-enoic acid, 9-hydroxyoctadecanoic acid, 10-hydroxyoctadecanoic acid, 9,10-dihydroxyoctadecanoic acid, 18-hydroxyoctadecanoic acid, 9,18-dihydroxyoctadecanoic acid, 10,18-dihydroxyoctadecanoic acid, 9,10,18-trihydroxyoctadecanoic acid, 9,10-epoxyoctadecanoic acid, (9Z)-octadec-9-enoic acid, (9E)-octadec-9-enoic acid, 18-hydroxy-9,10-dihydroxyoctadecanoic acid, 18-hydroxy-(9Z)-octadec-9-enoic acid, 18-hydroxy-(9E)-octadec-9-enoic acid, (13Z)-docosahexadec-13-enoic acid, (13E)-docosahexadec-13-enoic acid.

[0079] In some embodiments, the total amount of the one or more monoglycerides present is about 0.1% to about 20% by weight, about 0.1% to about 15% by weight, about 1% to about 30% by weight, about 1% to about 20% by weight, about 1% to about 15% by weight, about 5% to about 30% by weight, about 5% to about 25% by weight, or about 5% to about 15% by weight of the emulsion.

[0080] In some implementations, the emulsion also includes C4-C 28 One or more salts of fatty acids. In some embodiments, the emulsion contains C4-C... 28 A salt of fatty acids. In some embodiments, the emulsion contains C4-C... 28 Two, three, or more salts of fatty acids, such as C4-C 28 Two salts of fatty acids. In some embodiments, the salts include one or more salts of naturally occurring fatty acids.

[0081] In some implementations, the salt includes C6-C 28 Fatty acids, C8-C 28 Fatty acids, C4-C24 Fatty acids, C6-C 24 Fatty acids, C 12 -C 24 Fatty acids, C4-C 22 Fatty acids, C6-C 22 Fatty acids or C 12 -C 22 One or more salts of fatty acids. In some embodiments, the one or more salts include an unsubstituted side chain, such as an unsubstituted C. 12 -C 22 Side chain. In some embodiments, one or more salts include a straight-chain side chain, such as a straight-chain C. 12 -C 22 Side chain. In some embodiments, one or more salts include saturated side chains, such as saturated C. 12 -C 22 Side chain.

[0082] In some embodiments, the salt comprises one or more compounds of formula II.

[0083] (Formula II)

[0084] in:

[0085] R H It is C3-C 27 Side chain; and

[0086] X n+ It is a cation portion with a formal charge n.

[0087] In some embodiments, each of the one or more salts independently comprises a compound of formula II. In some embodiments of formula II, X n+ Selected from Li + Na + K + Cs + Ag + Ca 2+ Mg 2+ Zn 2+ Cu 2+ and (R) D )4N + In which R appears each time D Selected from H, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl, wherein each C1-C6 alkyl group is optionally surrounded by 1-3 R groups. E Replace, R E Independently selected from C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl groups. In some embodiments, X n+Yes (R) D )4N + One or more R D Together with the nitrogen atoms to which they are attached, they combine to form C3-C6 heterocyclic alkyl groups. In some embodiments of Formula II, X n+ Selected from Na + K + Ca 2+ Mg 2+ and Zn 2+ In some implementations of Formula II, R H It is a saturated side chain. In some embodiments of Formula II, R H It is an unsubstituted side chain. In some embodiments of Formula II, R H It is a straight-chain side chain. In some implementations of Formula II, R H It is C5-C 17 Side chain. In some embodiments of Formula II, R H It is C 11 -C 21 Side chain.

[0088] In some embodiments, the salt comprises one or more compounds of formula IIA.

[0089] (Formula IIA)

[0090] in:

[0091] R 1 R 2 R 3 ,R 4 R 5 ,R 6 R 7 R 8 and R 9 Each is independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy;

[0092] Each occurrence of R 10A R 10B R 11A and R 11B Independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy;

[0093] R on adjacent carbon atoms 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R9 R 10A R 10B R 11A and R 11B Any two of them can combine with the carbon atoms they are attached to to form a double bond, a 3- to 6-membered heterocyclic alkyl group, or a C3-C6 cycloalkyl group;

[0094] o is an integer between 0 and 17;

[0095] p is an integer between 0 and 17;

[0096] The sum of o and p is 0-17; and

[0097] X n+ It is a cation portion with a formal charge n.

[0098] In some embodiments, the one or more salts each independently comprise a compound of formula IIA. In some embodiments of formula IIA, X n+ Selected from Li + Na + K + Cs + Ag + Ca 2+ Mg 2+ Zn 2+ Cu 2+ and (R) D )4N + In which R appears each time D Selected from H, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl, wherein each C1-C6 alkyl group is optionally surrounded by 1-3 R groups. E Replace, R E Independently selected from C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl groups. In some embodiments, X n+ Yes (R) D )4N + and one or more R D Together with the nitrogen atoms to which they are attached, they combine to form C3-C6 heterocyclic alkyl groups. In some embodiments of Formula II, X n+ Selected from Na + K + Ca 2+ Mg 2+ and Zn 2+ .

[0099] In some implementations of Formula IIA, each R 1 R 2 R 3 R 4R 5 R 6 R 7 R 8 and R 9 , and each occurrence of R 10A R 10B R 11A and R 11B Independently selected from H and OH. In some embodiments of formula IIA, R on adjacent carbon atoms 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10A R 10B R 11A and R 11B Any two of them combine with the carbon atoms they are attached to to form ethylene oxide. In some embodiments of formula IIA, R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 , and each occurrence of R 10A R 10B R 11A and R 11B Two, one, or none of the atoms in the formula IIA are bonded together with the carbon atoms they are attached to to form a double bond. In some embodiments of formula IIA, R on adjacent carbon atoms 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 , and each occurrence of R 10A R 10B R 11A and R 11B One or none of them are bonded together with the carbon atoms they are attached to to form ethylene oxide. In some embodiments of formula IIA, R 1 R 2 R 3 R 4 R 5 R 6 R7 R 8 and R 9 And each time R appears 10A R 10B R 11A and R 11B Two, one, or none of them are OH.

[0100] In some implementations of Formula IIA, the sum of o and p is 0-13, 0-11, 0-9, 0-7, 5-17, 5-13, 5-11, 5-9, 5-7, 7-17, 7-13, 7-11, 7-9, 9-17, 9-13, 9-11, 11-17, or 11-13.

[0101] In some embodiments, the salt comprises one or more salts of saturated, straight-chain, unsubstituted fatty acids, such as sodium, potassium, silver, calcium, magnesium, or zinc salts. In some embodiments, the salt comprises one or more salts, such as sodium, potassium, silver, calcium, magnesium, or zinc salts of the following acids: heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, dodecanoic acid, 18-hydroxy-9,10-dihydroxyoctadecanoic acid, 18-hydroxy-(9Z)-octadec-9-enoic acid, or 18-hydroxy-(9E)-octadec-9-enoic acid.

[0102] In some embodiments, the total amount of one or more salts present is about 0.01 wt% to about 10 wt% of the emulsion, for example, about 0.01 wt% to about 5 wt%, about 0.01 wt% to about 3 wt%, about 0.1 wt% to about 10 wt%, about 0.1 wt% to about 5 wt%, about 0.1 wt% to about 3 wt%, about 0.5 wt% to about 10 wt%, about 0.5 wt% to about 5 wt%, or about 0.5 wt% to about 3 wt%. In some embodiments, the second phase comprises at least 50 wt% of the monoglycerides present in the emulsion, for example, at least 60 wt%, at least 70 wt%, at least 80 wt%, or at least 90 wt%. In some embodiments, the total weight ratio of one or more monoglycerides to the total weight of one or more salts is from about 100:1 to about 4:1, for example, from about 100:1 to about 6:1, from about 100:1 to about 8:1, from about 75:1 to about 4:1, from about 75:1 to about 6:1, from about 75:1 to about 8:1, from about 50:1 to about 4:1, from about 50:1 to about 6:1, or from about 50:1 to about 8:1.

[0103] In some embodiments, the emulsion further includes a surfactant. In some embodiments, the surfactant includes a nonionic surfactant. For example, in some embodiments, the surfactant includes polysorbates (e.g., polysorbate 80, polysorbate 20), ethoxylates (e.g., Triton...). TM X-100, Tergitol TM 15-S-9), sorbitol monooleate, sucrose monooleate, glyceryl monooleate, sucrose monolaurate, thuja alcohol, cocoside, or any combination thereof. For example, in some embodiments, the surfactant includes polysorbate 80. In some embodiments, the surfactant is present in a first phase, a second phase, or both. In some embodiments, the first phase comprises at least 50% by weight of the surfactant present in the emulsion, for example, at least 60% by weight, at least 70% by weight, at least 80% by weight, or at least 90% by weight.

[0104] In some embodiments, the weight ratio of the surfactant to the total amount of one or more essential oil components is from about 1:10 to about 10:1, for example, from about 1:10 to about 7.5:1, from about 1:10 to about 5:1, from about 1:10 to about 2.5:1, from about 1:7.5 to about 10:1, from about 1:7.5 to about 7.5:1, from about 1:7.5 to about 5:1, from about 1:7.5 to about 2.5:1, from about 1:5 to about 10:1, from about 1:5 to about 7.5:1, from about 1:5 to about 5:1, or from about 1:5 to about 2.5:1, from about 1:2.5 to about 10:1, from about 1:2.5 to about 7.5:1, from about 1:2.5 to about 5:1, or from about 1:2.5 to about 2.5:1.

[0105] In some embodiments, the total amount of surfactant present is about 0.001 wt% to about 10 wt% of the emulsion, for example, 0.001 wt% to about 7.5 wt%, about 0.001 wt% to about 5 wt%, about 0.01 wt% to about 10 wt%, about 0.01 wt% to about 7.5 wt%, about 0.01 wt% to about 5 wt%, about 0.1 wt% to about 10 wt%, about 0.1 wt% to about 7.5 wt%, or about 0.1 wt% to about 5 wt%.

[0106] In some embodiments, the aqueous medium comprises at least about 50% by weight of water, for example, at least about 60% by weight, at least about 70% by weight, at least about 80% by weight, at least about 90% by weight, or at least about 95% by weight of water. In some embodiments, the aqueous medium also includes methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, diethyl ether, methyl tert-butyl ether, or any combination thereof.

[0107] The emulsion described in this application may include one or more additional components, such as components that are non-toxic and safe for human and / or animal consumption. For example, the emulsion may include components that are direct or indirect food additives or food contact substances approved by the U.S. Food and Drug Administration (FDA), meet FDA regulatory requirements for use as food additives or food contact substances, or are components that the FDA generally considers safe (GRAS).

[0108] In some embodiments, the emulsion described in this application further comprises one or more fatty acids, such as C4-C 22 Fatty acids, or their esters, such as their C1-C6 alkyl esters. In some embodiments, the emulsion contains less than about 10% by weight, such as less than about 5% by weight, less than about 2% by weight, less than about 1% by weight, or is free of triglycerides, diglycerides, acetylated monoglycerides, lactylated monoglycerides, succinylated monoglycerides, sterols, bile acids, proteins, polysaccharides, phenols, lignans, aromatic acids, terpenoids, flavonoids, carotenoids, alkaloids, alcohols, alkanes, aldehydes, and any salts thereof.

[0109] Preparation method

[0110] This application also provides a method for preparing an emulsion. The method includes combining a first mixture at a first temperature and a second mixture at a second temperature to produce a third mixture, and stirring the third mixture to produce an emulsion. The first mixture contains one or more essential oil components and a surfactant, and the second mixture contains an aqueous medium and C4-C... 28 One or more monoglycerides of fatty acids. The emulsion comprises a first phase dispersed in an aqueous medium and a second phase dispersed in an aqueous medium, the first phase comprising one or more essential oil components and the second phase comprising one or more monoglycerides.

[0111] In some embodiments, the first mixture comprises one or more essential oil components and surfactants described in this application. In some embodiments, the method includes adding one or more essential oil components and surfactants to an aqueous medium under stirring to form the first mixture. In some such embodiments, forming the first mixture involves a catastrophic phase transition from an oil-in-water emulsion to a water-in-oil emulsion. In some embodiments, the water-in-oil emulsion may be further diluted with an aqueous medium to achieve a desired concentration.

[0112] In some embodiments, the second mixture comprises the aqueous medium described in this application and one or more glycerol monoesters described in this application. In some embodiments of the preparation method, the emulsion is the emulsion described in this application.

[0113] In some embodiments, the first temperature is from about 20°C to about 55°C, for example, from about 20°C to about 35°C, or from about 20°C to about 30°C. In some embodiments, the first temperature is about room temperature.

[0114] In some embodiments, the second temperature is higher than the Craft temperature of the second mixture. In some embodiments, the second temperature is at least about 60°C, for example at least about 65°C, or at least about 70°C. In some embodiments, the second temperature is about 60°C to about 75°C, about 60°C to about 70°C, about 65°C to about 75°C, or about 65°C to about 70°C. In some such embodiments, the method further includes cooling the third mixture to a third temperature less than about 55°C while stirring to produce a second phase dispersed in the aqueous medium. In other such embodiments, the method further includes cooling the emulsion to a third temperature less than about 55°C after stirring to produce a second phase dispersed in the aqueous medium. In some embodiments, the third temperature is lower than the Craft temperature of the second mixture. In some embodiments, the third temperature is less than about 50°C, less than about 40°C, less than about 35°C, or less than about 30°C. In some embodiments, the third temperature is about 20°C to about 55°C, for example, about 20°C to about 35°C, or about 20°C to about 30°C.

[0115] In some embodiments, the second temperature is lower than the Craft temperature of the second mixture. In some embodiments, the second temperature is lower than about 60°C, for example, lower than about 55°C, lower than about 50°C, lower than about 40°C, lower than about 35°C, or lower than about 30°C. In some embodiments, the second temperature is about 20°C to about 55°C, for example, about 20°C to about 35°C, or about 20°C to about 30°C. In some such embodiments, the method includes cooling the second mixture from a fourth temperature of at least about 65°C to the second temperature prior to combination to produce a second phase dispersed in an aqueous medium. In some embodiments, the second temperature is about 20°C to about 55°C, for example, about 20°C to about 30°C, or about 30°C to about 55°C. In some embodiments, the fourth temperature is higher than the Craft temperature of the second mixture. In some embodiments, the fourth temperature is at least about 70°C. In some embodiments, the fourth temperature is about 65°C to about 75°C.

[0116] In some embodiments of the preparation method, the first phase comprises droplets with an average diameter of about 10 nm to about 1,000 nm, for example, about 10 nm to about 500 nm, about 10 nm to about 300 nm, about 25 nm to about 1,000 nm, about 25 nm to about 500 nm, about 25 nm to about 300 nm, about 50 nm to about 1,000 nm, about 50 nm to about 500 nm, or about 50 nm to about 300 nm. In some embodiments of the preparation method, the first phase comprises droplets with a d90 diameter distribution of up to about 500 nm, for example, up to about 450 nm, up to about 400 nm, up to about 350 nm, up to about 300 nm, or up to about 250 nm.

[0117] In some embodiments of the preparation method, one or more essential oil components include lavender oil, rose oil, ylang-ylang oil, eucalyptus oil, sweet orange oil, chamomile oil, peppermint oil, jasmine oil, lemon oil, lemongrass oil, tea tree oil, frankincense oil, grapefruit oil, clove oil, cinnamon oil, vanilla oil, rosemary oil, white tea oil, bergamot oil, sage oil, laurel oil, geranium oil, patchouli oil, sandalwood oil, immortelle oil, oregano oil, pine needle oil, eucalyptus cone oil, camphor oil, benzoin oil, fennel oil, thyme oil, nutmeg oil, lemon eucalyptus oil, ravensara leaf oil, wild orange oil, myrrh oil, osmanthus oil, cypress oil, artemisia oil, basil oil, vetiver oil, juniper spearmint oil, lemon balm oil, ginger oil, gardenia oil, lotus seed oil, neroli oil, palmarosa oil, mandarin orange oil, and citronella oil. Oils such as litsea cubeba oil, rosewood oil, valerian oil, verbena oil, cypress oil, lime pepper oil, magnolia oil, or any combination thereof. For example, in some embodiments of the preparation method, one or more essential oil components include rosemary oil, ylang-ylang oil, cinnamon bark oil, cinnamon leaf oil, or any combination thereof. In some embodiments of the preparation method, one or more essential oil components include citral, methyl eugenol, 2-methoxycinnamonaldehyde, trans-cinnamonaldehyde, trans, trans-2,4-decanoic acid, benzaldehyde, 1,8-cineole, α-pinene, or any combination thereof. In some embodiments of the preparation method, one or more essential oil components include trans-cinnamonaldehyde and rosemary oil. In some embodiments of the preparation method, one or more essential oil components include trans-cinnamonaldehyde, methyl eugenol, and citral.

[0118] In some embodiments, the total amount of one or more essential oil components present in the first mixture is about 30% to about 70% by weight of the first mixture, for example, about 30% to about 60% by weight, about 40% to about 70% by weight, or about 40% to about 60% by weight.

[0119] In some embodiments of the preparation method, the surfactant includes the nonionic surfactant described in this application. In some embodiments, the total amount of the surfactant present in the first mixture is from about 30% to about 70% by weight of the first mixture, for example, from about 30% to about 60% by weight, from about 40% to about 70% by weight, or from about 40% to about 60% by weight. In some embodiments of the preparation method, the weight ratio of the surfactant to the total amount of one or more essential oil components is from about 1:10 to about 10:1, for example, from about 1:10 to about 7.5:1, from about 1:10 to about 5:1, from about 1:10 to about 2.5:1, from about 1:7.5 to about 10:1, from about 1:7.5 to about 7.5:1, from about 1:7.5 to about 5:1, from about 1:7.5 to about 2.5:1, from about 1:5 to about 10:1, from about 1:5 to about 7.5:1, from about 1:5 to about 5:1, or from about 1:5 to about 2.5:1, from about 1:2.5 to about 10:1, from about 1:2.5 to about 7.5:1, from about 1:2.5 to about 5:1, or from about 1:2.5 to about 2.5:1.

[0120] In some embodiments of the preparation method, the second phase comprises vesicles containing one or more monoglycerides. In some embodiments of the preparation method, the second phase comprises vesicles with an average diameter of about 10 nm to about 1,000 nm, for example, about 10 nm to about 500 nm, about 10 nm to about 200 nm, about 50 nm to about 1,000 nm, about 50 nm to about 500 nm, about 50 nm to about 200 nm, about 100 nm to about 1,000 nm, about 100 nm to about 500 nm, or about 100 nm to about 200 nm. In some embodiments of the preparation method, the second phase comprises vesicles with a d90 diameter distribution of up to about 900 nm, for example, up to about 800 nm, up to about 700 nm, up to about 600 nm, up to about 500 nm, or up to about 450 nm.

[0121] In some embodiments of the preparation method, the monoglycerides include compounds of formula Ii, I-ii, IA-I, or IA-II as described in this application. In some embodiments, the total amount of one or more monoglycerides present in the second mixture is from about 0.1 wt% to about 30 wt% of the second mixture, for example, from about 0.1 wt% to about 20 wt%, from about 0.1 wt% to about 15 wt%, from about 1 wt% to about 30 wt%, from about 1 wt% to about 20 wt%, from about 1 wt% to about 15 wt%, from about 5 wt% to about 30 wt%, from about 5 wt% to about 25 wt%, or from about 5 wt% to about 15 wt%.

[0122] In some embodiments, the second mixture further includes C4–C 28One or more salts of fatty acids. In some embodiments of the preparation method, the salts include compounds of formula II or IIA as described in this application. In some embodiments, the total amount of one or more salts present in the second mixture is from about 0.01 wt% to about 10 wt% of the second mixture, for example, from about 0.01 wt% to about 5 wt%, from about 0.01 wt% to about 3 wt%, from about 0.1 wt% to about 10 wt%, from about 0.1 wt% to about 5 wt%, from about 0.1 wt% to about 3 wt%, from about 0.5 wt% to about 10 wt%, from about 0.5 wt% to about 5 wt%, or from about 0.5 wt% to about 3 wt%. In some embodiments of the preparation method, the total weight ratio of one or more glycerol monoesters to the total weight of one or more salts is about 100:1 to about 4:1, for example, about 100:1 to about 6:1, about 100:1 to about 8:1, about 75:1 to about 4:1, about 75:1 to about 6:1, about 75:1 to about 8:1, about 50:1 to about 4:1, about 50:1 to about 6:1, or about 50:1 to about 8:1.

[0123] Coating method

[0124] This application also provides a method for coating agricultural products. In some embodiments, the coating method includes contacting the surface of the agricultural product with the emulsion described in this application and removing at least a portion of the aqueous medium to form a coating on the surface of the agricultural product.

[0125] In some embodiments, the coating method includes contacting the surface of the agricultural product with a first emulsion and a second emulsion. The first emulsion comprises a first aqueous medium and a first phase dispersed in the first aqueous medium, the first phase comprising one or more essential oil components, and the second emulsion comprises a second aqueous medium and a second phase dispersed in the second aqueous medium, the second phase comprising C4–C 28 One or more monoglycerides of fatty acids.

[0126] In some embodiments, the first aqueous medium is the aqueous medium described in this application. In some embodiments, the second aqueous medium is the aqueous medium described in this application. In some embodiments, the first aqueous medium and the second aqueous medium are the same. In some embodiments, the first aqueous medium and the second aqueous medium each independently contain at least about 50% by weight of water, for example, at least about 60% by weight, at least about 70% by weight, at least about 80% by weight, at least about 90% by weight, or at least about 95% by weight of water. In some embodiments, one or both of the first aqueous medium and the second aqueous medium independently further include methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, diethyl ether, methyl tert-butyl ether, or any combination thereof.

[0127] In some embodiments of the coating method, the first emulsion comprises the first phase described in this application. For example, in some embodiments of the coating method, the first phase comprises droplets with an average diameter of about 10 nm to about 1,000 nm, such as about 10 nm to about 500 nm, about 10 nm to about 300 nm, about 25 nm to about 1,000 nm, about 25 nm to about 500 nm, about 25 nm to about 300 nm, about 50 nm to about 1,000 nm, about 50 nm to about 500 nm, or about 50 nm to about 300 nm. In some embodiments of the coating method, the first phase comprises droplets with a d90 diameter distribution of up to about 500 nm, such as up to about 450 nm, up to about 400 nm, up to about 350 nm, up to about 300 nm, or up to about 250 nm.

[0128] In some embodiments of the coating method, one or more essential oil components include lavender oil, rose oil, ylang-ylang oil, eucalyptus oil, sweet orange oil, chamomile oil, peppermint oil, jasmine oil, lemon oil, lemongrass oil, tea tree oil, frankincense oil, grapefruit oil, clove oil, cinnamon oil, vanilla oil, rosemary oil, white tea oil, bergamot oil, sage oil, laurel oil, geranium oil, patchouli oil, sandalwood oil, immortelle oil, oregano oil, pine needle oil, eucalyptus cone oil, camphor oil, benzoin oil, fennel oil, thyme oil, nutmeg oil, lemon eucalyptus oil, ravensa leaf oil, wild orange oil, myrrh oil, osmanthus oil, cypress oil, artemisia oil, basil oil, vetiver oil, juniper spearmint oil, lemon balm oil, ginger oil, gardenia oil, lotus seed oil, neroli oil, palmarosa oil, mandarin orange oil, and citronella oil. Oils such as litsea cubeba oil, rosewood oil, valerian oil, verbena oil, cypress oil, lime pepper oil, magnolia oil, or any combination thereof. For example, in some embodiments of the coating method, one or more essential oil components include rosemary oil, ylang-ylang oil, cinnamon bark oil, cinnamon leaf oil, or any combination thereof. In some embodiments of the coating method, one or more essential oil components include citral, methyl eugenol, 2-methoxycinnamaldehyde, trans-cinnamaldehyde, trans, trans-2,4-decanoic acid, benzaldehyde, 1,8-cineole, α-pinene, or any combination thereof. In some embodiments of the coating method, one or more essential oil components include trans-cinnamaldehyde and rosemary oil. In some embodiments of the coating method, one or more essential oil components include trans-cinnamaldehyde, methyl eugenol, and citral.

[0129] In some embodiments of the coating method, the total amount of one or more essential oil components present in the first emulsion is from about 0.001% by weight to about 20% by weight of the first emulsion, for example, from about 0.001% by weight to about 10% by weight of the first emulsion, from about 0.01% by weight to about 7.5% by weight of the first emulsion, or from about 0.01% by weight to about 5% by weight of the first emulsion.

[0130] In some embodiments of the coating method, the first emulsion further includes a surfactant. In some such embodiments, the surfactant includes the nonionic surfactant described in this application. In some embodiments, the total amount of the surfactant present in the first emulsion is from about 0.001 wt% to about 20 wt% of the first emulsion, for example, from about 0.001 wt% to about 10 wt%, from about 0.01 wt% to about 7.5 wt%, or from about 0.01 wt% to about 5 wt% of the first emulsion. In some embodiments of the coating method, the weight ratio of the surfactant to the total amount of one or more essential oil components in the first emulsion is from about 1:10 to about 10:1, for example, from about 1:10 to about 7.5:1, from about 1:10 to about 5:1, from about 1:10 to about 2.5:1, from about 1:7.5 to about 10:1, from about 1:7.5 to about 7.5:1, from about 1:7.5 to about 5:1, from about 1:7.5 to about 2.5:1, from about 1:5 to about 10:1, from about 1:7.5 to about 5:1, from about 1:7.5 to about 2.5:1, from about 1:5 to about 10:1, from about 1:5 to about 7.5:1, from about 1:5 to about 5:1, or from about 1:5 to about 2.5:1, from about 1:2.5 to about 10:1, from about 1:2.5 to about 7.5:1, from about 1:2.5 to about 5:1, or from about 1:2.5 to about 2.5:1.

[0131] In some embodiments of the coating method, the second emulsion comprises the second phase described in this application. For example, in some embodiments of the coating method, the second phase comprises vesicles containing one or more monoglycerides. In some embodiments of the coating method, the second phase comprises vesicles with an average diameter of about 10 nm to about 1,000 nm, such as about 10 nm to about 500 nm, about 10 nm to about 200 nm, about 50 nm to about 1,000 nm, about 50 nm to about 500 nm, about 50 nm to about 200 nm, about 100 nm to about 1,000 nm, about 100 nm to about 500 nm, or about 100 nm to about 200 nm. In some embodiments of the preparation method, the second phase comprises vesicles with a d90 diameter distribution of up to about 900 nm, such as up to about 800 nm, up to about 700 nm, up to about 600 nm, up to about 500 nm, or up to about 450 nm.

[0132] In some embodiments of the coating method, the monoglycerides include compounds of formula Ii, I-ii, IA-i, or IA-ii as described in this application. In some embodiments, one or more monoglycerides are present in the second emulsion in an amount from about 0.1% to about 30% by weight of the second emulsion, for example, from about 0.1% to about 20% by weight, from about 0.1% to about 15% by weight, from about 1% to about 30% by weight, from about 1% to about 20% by weight, from about 1% to about 15% by weight, from about 5% to about 30% by weight, from about 5% to about 25% by weight, or from about 5% to about 15% by weight.

[0133] In some embodiments, the second emulsion further includes C4–C 28 One or more salts of fatty acids. In some embodiments of the coating method, the salts include compounds of formula II or IIA as described in this application. In some embodiments, the total amount of one or more salts present in the second emulsion is from about 0.01% to about 10% by weight of the second emulsion, for example, from about 0.01% to about 5% by weight, from about 0.01% to about 3% by weight, from about 0.1% to about 10% by weight, from about 0.1% to about 5% by weight, from about 0.1% to about 3% by weight, from about 0.5% to about 10% by weight, from about 0.5% to about 5% by weight, or from about 0.5% to about 3% by weight. In some embodiments of the preparation method, the weight ratio of the total amount of one or more monoglycerides to the total amount of one or more salts in the second emulsion is from about 100:1 to about 4:1, for example, from about 100:1 to about 6:1, from about 100:1 to about 8:1, from about 75:1 to about 4:1, from about 75:1 to about 6:1, from about 75:1 to about 8:1, from about 50:1 to about 4:1, from about 50:1 to about 6:1, or from about 50:1 to about 8:1.

[0134] In some embodiments, the method includes contacting the surface of the agricultural product with a first emulsion and removing at least a portion of the first aqueous medium to create a treated surface of the agricultural product, and then contacting the treated surface with a second emulsion and removing at least a portion of the second aqueous medium to form a coating on the treated surface. In some embodiments, the surface of the agricultural product is contacted with the first emulsion one or more days prior to contacting the treated surface with the second emulsion. For example, in some such embodiments, the surface of the agricultural product is contacted with the first emulsion before harvest, and the treated surface is contacted with the second emulsion at or after harvest. In some embodiments, the surface of the agricultural product is contacted with the first emulsion less than one day prior to contacting the treated surface with the second emulsion. In some such embodiments, the surface of the agricultural product is contacted with the first emulsion after harvest, and then the treated surface is contacted with the second emulsion, for example, within 12 hours, 6 hours, 4 hours, 2 hours, or 1 hour after the formation of the treated surface.

[0135] In some embodiments, the method includes contacting the surface of the agricultural product with a first emulsion and a second emulsion, and then removing at least a portion of the first aqueous medium and at least a portion of the second aqueous medium to form a coating on the surface of the agricultural product. In some such embodiments, the method includes mixing the first emulsion and the second emulsion and contacting the mixture with the surface of the agricultural product. In other such embodiments, the method includes simultaneously contacting the surface of the agricultural product with the first emulsion and the second emulsion, or sequentially contacting the surface of the agricultural product with the first emulsion and the second emulsion before removing at least a portion of the first aqueous medium or the second aqueous medium.

[0136] In some embodiments of the coating method, the agricultural product is an edible agricultural product, including, for example, fruits, vegetables, edible seeds and nuts, herbs, spices, agricultural products, meat, eggs, dairy products, seafood, grains, or any other consumer goods. In other embodiments of the coating method, the agricultural product is an inedible agricultural product, including, for example, inedible flowers, seeds, buds, stems, leaves, whole plants, etc. In some embodiments, the method includes contacting the outer surface of the agricultural product (e.g., the cuticle surface) with the emulsion.

[0137] In some embodiments of the coating method, contact with the surface of the agricultural product includes spraying an emulsion onto the surface of the agricultural product. The emulsion may be sprayed, for example, from a commercially available sprayer. In some embodiments, an emulsion aerosol is sprayed onto the surface of the agricultural product. In some embodiments of the coating method, contact with the surface of the agricultural product includes immersing the agricultural product in the emulsion. In other embodiments of the coating method, the emulsion may be brushed, dripped, drip-cast, rolled, lightly coated, or poured onto the surface of the agricultural product.

[0138] In some embodiments of the coating method, removing at least a portion of the aqueous medium includes evaporating at least a portion of the aqueous medium. In some embodiments, evaporation can be passive. In other embodiments, evaporation can be active, for example, as in convection drying.

[0139] coating

[0140] This application also provides coated agricultural products, comprising a layer formed by the coating method described in this application and placed on the surface of the agricultural product. In some embodiments, the agricultural product is an edible agricultural product, including, for example, fruits, vegetables, edible seeds and nuts, herbs, spices, agricultural products, meat, eggs, dairy products, seafood, grains, or any other consumer product. In other embodiments, the agricultural product is an inedible agricultural product, including, for example, inedible flowers, seeds, buds, stems, leaves, whole plants, etc. In some embodiments, the layer is disposed on the outer surface of the agricultural product (e.g., the cuticle surface).

[0141] In some embodiments, the thickness of the layer is from about 0.1 μm to about 20 μm, for example, from about 0.1 μm to about 15 μm, from about 0.1 μm to about 10 μm, from about 0.5 μm to about 20 μm, from about 0.5 μm to about 15 μm, from about 0.5 μm to about 10 μm, from about 1 μm to about 20 μm, from about 1 μm to about 15 μm, or from about 1 μm to about 10 μm.

[0142] Example

[0143] Example 1. Lemon Treatment

[0144] Mixture A was prepared comprising a 500 g / L essential oil blend in polysorbate 80, the essential oil blend comprising methyl eugenol, trans-cinnamaldehyde, and citral (1:1:1, volume ratio). Emulsions AC comprising 30 g / L, 3 g / L, and 0.3 g / L of mixture A, respectively, were prepared by slowly adding mixture A to DI water while stirring at 800 rpm until combined.

[0145] A Wyatt Technology Dynapro Nanostar Laser Photometer, WDPN-12 model, was used, running DYNAMICS V7.10.1.21 (correlation function 1.50-60,000 μs; peak radius 0.50-10,000 nm; minimum peak intensity 1%; 5 s acquisition time; 1 s readout interval; 90 The droplet size distribution of representative essential oil emulsions was measured using the detector angle. The results shown in Table 1 indicate that the emulsions contain nanoscale droplets of essential oil components.

[0146] Table 1. Droplet size distribution of representative emulsions.

[0147]

[0148] California lemons were inoculated with 100–1,000 Penicillium finger spores and then treated by dip-in with one of the emulsions AC or a control solution containing 1 g / L imidacloprid (“IMZ”). The infection rate of the treated lemons and the control group of untreated lemons was then measured over 8 days.

[0149] The results shown in Table 2 indicate that treatment with emulsion AC reduced Penicillium finger infection in lemons.

[0150] Table 2. Infection rate after lemon inoculation

[0151]

[0152] Example 2. Emulsion preparation - Adding at room temperature

[0153] Mixture A was prepared according to Example 1. Mixture B was also prepared, comprising 120 g / L of a coating agent comprising 95 wt% glyceryl monostearate (an equilibrium mixture of 2,3-dihydroxypropyl-1-yloctadecanoate and 1,3-dihydroxypropyl-2-yloctadecanoate in a molar ratio of about 90:10) and 5 wt% sodium stearate in a DI aqueous solution. Mixture B was heated to above its Craft temperature with stirring, and then cooled to room temperature below its Craft temperature without stirring.

[0154] Emulsions 1-4, each comprising 0.5 g / L, 1 g / L, 10 g / L, and 30 g / L mixture A, were each prepared by adding mixture A dropwise to 100 mL of cooled mixture B while stirring at 400 rpm, followed by stirring at 400 rpm for another 5 minutes. Each of emulsions 1-4 was stable for at least 1 day.

[0155] Example 3. Emulsion preparation - Adding at 50°C

[0156] Mixture A was prepared according to Example 1. Mixture B was prepared according to Example 2. Mixture B was heated to above its Craft temperature with stirring, and then cooled to 50°C below its Craft temperature without stirring.

[0157] Emulsion 5, containing 0.5 g / L of mixture A, was prepared by adding mixture A dropwise to 100 mL of mixture B at 50 °C while stirring at 400 rpm, followed by stirring at 400 rpm for another 5 minutes. Emulsion 5 was stable for at least 1 day.

[0158] Example 4. Emulsion preparation - Adding at 70°C

[0159] Mixture A was prepared according to Example 1. Mixture B was prepared according to Example 2. Mixture B was heated to above its Craft temperature with stirring, and then cooled to 70°C above its Craft temperature without stirring.

[0160] Emulsion 6, containing 0.5 g / L of mixture A, was prepared by adding mixture A dropwise to 100 mL of mixture B at 70 °C while stirring at 400 rpm, followed by stirring at 400 rpm for another 10 minutes, and then cooling the mixture to 50 °C, below the Kraft temperature of mixture B. Emulsion 6 was stable for at least 1 day.

[0161] Example 5. Emulsion preparation - addition and stirring at 65°C

[0162] Mixture A was prepared according to Example 1. Mixture B was prepared according to Example 2. Mixture B was heated to above its Craft temperature with stirring, and then cooled to 65°C above its Craft temperature without stirring.

[0163] Emulsion 7, containing 0.5 g / L of mixture A, was prepared by adding mixture A dropwise to 100 mL of mixture B at 65 °C while stirring and heating at 400 rpm to maintain the temperature of the mixture, stirring and heating at 400 rpm for an additional 15 minutes, and then cooling the mixture to a temperature below the Craft temperature of mixture B without stirring. Emulsion 7 was stable for at least 1 day.

[0164] Example 6. Emulsion Preparation

[0165] Mixture C, comprising polysorbate 80, trans-cinnamaldehyde, and rosemary oil (2:1:1, w / v), is prepared by stirring until homogeneous. Emulsion D is prepared by adding an equal volume of water to mixture C under stirring. An oil-in-water (O / W) emulsion is initially formed, followed by a catastrophic phase transition, completely transforming into a water-in-oil (W / O) emulsion. The resulting emulsion exhibits near-neutral buoyancy and demonstrates acceptable homogeneity, stability, and antimicrobial efficacy. The emulsion can be diluted in water under stirring until the desired concentration is achieved, for example, for coating agricultural products.

[0166] Although this disclosure contains numerous details of specific embodiments, these details should not be construed as limiting the scope of the subject matter or the scope of the claims, but rather as descriptions of features that may be specific to particular embodiments. Certain features described in this disclosure in the context of a single embodiment may also be implemented in combination in a single embodiment. Conversely, various features described in the context of a single embodiment may also be implemented individually or in any suitable sub-combination in multiple embodiments. Furthermore, although previously described features may be described as functioning in certain combinations and even initially claimed in this way, in some cases, one or more features from the claimed combination may be removed from the combination, and the claimed combination may be for sub-combinations or variations thereof.

[0167] Specific embodiments of the subject matter have been described. Other embodiments, variations, and substitutions of the described embodiments are within the scope of this disclosure. It will be apparent to those skilled in the art that any one or more of the appended claims are applicable. Although operations are depicted in a specific order in the drawings or claims, this should not be construed as requiring that these operations be performed in the specific order shown or sequentially, or that all of the shown operations (some operations may be considered optional) to achieve the desired result.

[0168] Therefore, the exemplary embodiments described above do not limit or restrict the scope of this invention. Other changes, substitutions, and modifications are possible without departing from the spirit and scope of this invention.

Claims

1. An emulsion comprising: Aqueous media; The first phase dispersed in the aqueous medium; and The second phase dispersed in this aqueous medium, in: The first phase comprises one or more essential oil components, present in a total amount of about 0.001% to about 10% by weight of the emulsion; and The second phase contains C4–C 28 One or more glycerol monoesters of fatty acids, present in a total amount of about 0.1% to about 30% by weight of the emulsion.

2. The emulsion of claim 1, wherein the first phase comprises droplets with an average diameter of about 10 nm to about 1,000 nm.

3. The emulsion according to claim 1, wherein the first phase comprises droplets with an average diameter of about 50 nm to about 300 nm.

4. The emulsion according to any one of claims 1-3, wherein the first phase comprises droplets having a d90 diameter distribution of up to about 500 nm.

5. The emulsion according to any one of claims 1-3, wherein the first phase comprises droplets having a d90 diameter distribution of up to about 350 nm.

6. The emulsion according to any one of claims 1-5, wherein the one or more essential oil components include lavender oil, rose oil, ylang-ylang oil, eucalyptus oil, sweet orange oil, chamomile oil, peppermint oil, jasmine oil, lemon oil, lemongrass oil, tea tree oil, frankincense oil, grapefruit oil, clove oil, cinnamon oil, vanilla oil, rosemary oil, white tea oil, bergamot oil, sage oil, laurel oil, geranium oil, patchouli oil, sandalwood oil, immortelle oil, oregano oil, pine needle oil, eucalyptus cone oil, camphor oil, benzoin oil, fennel oil, thyme oil, nutmeg oil, lemon eucalyptus oil, ravensara leaf oil, wild orange oil, myrrh oil, osmanthus oil, cypress oil, artemisia oil, basil oil, vetiver oil, juniper spearmint oil, lemon balm oil, ginger oil, gardenia oil, lotus seed oil, neroli oil, palmarosa oil, mandarin orange oil, and citronella oil. Litsea cubeba oil, redwood oil, valerian oil, verbena oil, cypress oil, lime pepper oil, magnolia oil, or any combination thereof.

7. The emulsion according to any one of claims 1-5, wherein the one or more essential oil components comprise rosemary oil, ylang-ylang oil, cinnamon bark oil, cinnamon leaf oil, or any combination thereof.

8. The emulsion according to any one of claims 1-7, wherein the one or more essential oil components comprise citral, methyl eugenol, 2-methoxycinnamaldehyde, trans-cinnamaldehyde, trans, trans-2,4-decanoic acid, benzaldehyde, 1,8-cineole, α-pinene, or any combination thereof.

9. The emulsion according to any one of claims 1-8, wherein one or more essential oil components comprise trans-cinnamaldehyde and rosemary oil.

10. The emulsion according to any one of claims 1-8, wherein the one or more essential oil components comprise trans-cinnamaldehyde, methyl eugenol, and citral.

11. The emulsion according to any one of claims 1-10, wherein the total amount of the one or more essential oil components is from about 0.01% by weight to about 7.5% by weight of the emulsion.

12. The emulsion according to any one of claims 1-10, wherein the total amount of the one or more essential oil components is from about 0.01% by weight to about 5% by weight of the emulsion.

13. The emulsion according to any one of claims 1-12 further comprises a surfactant, which is present in an amount of about 0.001% by weight to about 10% by weight of the emulsion.

14. The emulsion of claim 13, wherein the surfactant comprises a nonionic surfactant.

15. The emulsion of claim 14, wherein the surfactant comprises polysorbate.

16. The emulsion according to any one of claims 13-15, wherein the weight ratio of the surfactant to the total amount of the one or more essential oil components is from about 0.1:1 to about 10:

1.

17. The emulsion according to any one of claims 13-15, wherein the weight ratio of the surfactant to the total amount of the one or more essential oil components is from about 0.5:1 to about 1:0.

5.

18. The emulsion according to any one of claims 13-17, wherein the total amount of the surfactant is from about 0.01% by weight to about 7.5% by weight of the emulsion.

19. The emulsion according to any one of claims 13-17, wherein the total amount of the surfactant is from about 0.01% by weight to about 5% by weight of the emulsion.

20. The emulsion according to any one of claims 1-19, wherein the second phase comprises vesicles with an average diameter of about 100 nm to about 200 nm.

21. The emulsion according to any one of claims 1-20, wherein the second phase comprises vesicles having a d90 diameter distribution of up to about 450 nm.

22. The emulsion according to any one of claims 1-21, wherein each of the one or more glycerol monoesters independently comprises a compound of formula Ii or formulas I-ii: (Formula II) (Formula I-ii) in: R A1 and R A2 Each is independently selected from H and C1-C6 alkyl groups; and R H It is C3-C 27 Side chain.

23. The emulsion according to claim 22, wherein R A1 and R A2 Each is represented by H.

24. The emulsion according to claim 22 or 23, wherein R H It is a saturated, unsubstituted side chain.

25. The emulsion according to any one of claims 22-24, wherein R H It is C 11 –C 21 Side chain.

26. The emulsion according to any one of claims 22-25, wherein the one or more monoglycerides comprise: The first compound of formula Ii or formula I-ii, wherein R H It is C 15 –C 27 Side chain; and The second compound of formula Ii or formula I-ii, wherein R H It is C3–C 13 Side chain.

27. The emulsion according to any one of claims 1-21, wherein each of the one or more glycerol monoesters independently comprises a compound of formula IA-i or formula IA-ii: (Formula IA-i) (Formula IA-ii) in: R A1 and R A2 Each is independently selected from H and C1-C6 alkyl groups; R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 and R 9 Each is independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy; Each occurrence of R 10A R 10B R 11A and R 11B Independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy; R on adjacent carbon atoms 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10A R 10B R 11A and R 11B Any two of them can combine with the carbon atoms they are attached to to form a double bond, a 3- to 6-membered heterocyclic alkyl group, or a C3-C6 cycloalkyl group; o is an integer between 0 and 17; p is an integer between 0 and 17; and The sum of o and p is 0-17.

28. The emulsion of claim 27, wherein R A1 and R A2 Each is represented by H.

29. The emulsion according to any one of claims 1-28, wherein the total amount of the one or more monoglycerides is about 1% to about 30% by weight of the emulsion.

30. The emulsion according to any one of claims 1-28, wherein the total amount of the one or more monoglycerides is about 5% to about 20% by weight of the emulsion.

31. The emulsion according to any one of claims 1-30, wherein the emulsion further comprises C4–C 28 One or more salts of fatty acids, present in a total amount of 0.01% to about 10% by weight of the emulsion.

32. The emulsion of claim 31, wherein each of the one or more salts independently comprises a compound of formula II: (Formula II) in: R H It is C3-C 27 Side chain; and X n+ It is a cation portion with a formal charge n.

33. The emulsion according to claim 32, wherein X n+ Selected from Li + Na + K + Cs + Ag + Ca 2+ Mg 2+ Zn 2+ Cu 2+ and (R) D )4N + ,and Each occurrence of R D Selected from H, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl, wherein Each C1-C6 alkyl group is optionally surrounded by 1-3 R groups. E Replace, R E Independently selected from C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl; and Optionally, one or more R D They combine with the nitrogen atoms to which they are attached to form C3-C6 heterocyclic alkyl groups.

34. The emulsion according to claim 32 or 33, wherein R H It is a saturated, unsubstituted side chain.

35. The emulsion according to claim 31, wherein each of the one or more salts independently comprises a compound of formula IIA: (Formula IIA) in: R 1 R 2 R 3 ,R 4 R 5 ,R 6 R 7 R 8 and R 9 Each is independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy; Each occurrence of R 10A R 10B R 11A and R 11B Independently selected from H, OH, C1-C6 alkyl, C2-C6 alkenyl, and C1-C6 alkoxy; R on adjacent carbon atoms 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 R 9 R 10A R 10B R 11A and R 11B Any two of them can combine with the carbon atoms they are attached to to form a double bond, a 3- to 6-membered heterocyclic alkyl group, or a C3-C6 cycloalkyl group; o is an integer between 0 and 17; p is an integer between 0 and 17; The sum of o and p is 0-17; and X n+ It is a cation portion with a formal charge n.

36. The emulsion according to claim 35, wherein X n+ Selected from Li + Na + K + Cs + Ag + Ca 2+ Mg 2+ Zn 2+ Cu 2+ and (R) D )4N + ,and Each occurrence of R D Selected from H, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl, wherein Each C1-C6 alkyl group is optionally surrounded by 1-3 R groups. E Replace, R E Independently selected from C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl; and Optionally, one or more R D They combine with the nitrogen atoms to which they are attached to form C3-C6 heterocyclic alkyl groups.

37. The emulsion according to any one of claims 31-34, wherein the total amount of the one or more monoglycerides is in a weight ratio of about 100:1 to about 4:1 to the total amount of the one or more salts.

38. The emulsion according to any one of claims 31-36, wherein the total amount of the one or more monoglycerides is in a weight ratio of about 50:1 to about 6:1 to the total amount of the one or more salts.

39. The emulsion according to any one of claims 31-38, wherein the total amount of the one or more salts is from about 0.1% by weight to about 5% by weight of the emulsion.

40. The emulsion according to any one of claims 31-38, wherein the total amount of the one or more salts is from about 0.1% to about 3% by weight of the emulsion.

41. The emulsion according to any one of claims 1-40, wherein the aqueous medium further comprises methanol, ethanol, isopropanol, butanol, acetone, ethyl acetate, chloroform, acetonitrile, tetrahydrofuran, diethyl ether, methyl tert-butyl ether, or any combination thereof.

42. A method for preparing an emulsion, comprising: A first mixture at a first temperature and a second mixture at a second temperature are combined to produce a third mixture, wherein the first mixture contains one or more essential oil components and surfactants, and the second mixture contains an aqueous medium and C4–C. 28 One or more monoglycerides of fatty acids; and The third mixture is stirred to produce an emulsion, wherein the emulsion comprises: A first phase dispersed in the aqueous medium, the first phase comprising one or more essential oil components; and A second phase dispersed in the aqueous medium, the second phase comprising one or more glycerol monoesters.

43. The method of claim 42, wherein the second temperature is at least about 60°C.

44. The method of claim 43 further comprises, while stirring, cooling the third mixture to a third temperature below about 55°C to produce a second phase dispersed in the aqueous medium.

45. The method of claim 43 further comprises, after stirring, cooling the emulsion to a third temperature below about 55°C to produce a second phase dispersed in the aqueous medium.

46. ​​The method of claim 42, wherein the second temperature is below about 60°C.

47. The method of claim 46, further comprising, prior to combination, cooling the second mixture from a fourth temperature of at least about 65°C to a second temperature to produce the second phase dispersed in the aqueous medium.

48. The method of claim 47, wherein the second temperature is about 20°C to about 30°C.

49. The method of claim 47, wherein the second temperature is about 30°C to about 55°C.

50. The method according to any one of claims 42-49, wherein the first phase comprises droplets with an average diameter of about 10 nm to about 1,000 nm.

51. The method according to any one of claims 42-49, wherein the first phase comprises droplets with an average diameter of about 50 nm to about 300 nm.

52. The method according to any one of claims 42 to 51, wherein the first phase comprises droplets having a d90 diameter distribution of up to about 500 nm.

53. The method according to any one of claims 42-52, wherein the first phase comprises droplets having a d90 diameter distribution of up to about 350 nm.

54. The method according to any one of claims 42-53, wherein the one or more essential oil components include lavender oil, rose oil, ylang-ylang oil, eucalyptus oil, sweet orange oil, chamomile oil, peppermint oil, jasmine oil, lemon oil, lemongrass oil, tea tree oil, frankincense oil, grapefruit oil, clove oil, cinnamon oil, vanilla oil, rosemary oil, white tea oil, bergamot oil, sage oil, laurel oil, geranium oil, patchouli oil, sandalwood oil, immortelle oil, oregano oil, pine needle oil, eucalyptus cone oil, camphor oil, benzoin oil, fennel oil, thyme oil, nutmeg oil, lemon eucalyptus oil, ravensara leaf oil, wild orange oil, myrrh oil, osmanthus oil, cypress oil, artemisia oil, and basil oil. (oil), vetiver oil, juniper spearmint oil, lemon balm oil, ginger oil, gardenia oil, lotus seed oil, neroli oil, palmarosa oil, mandarin orange oil, citronella oil, litsea cubeba oil, redwood oil, valerian oil, verbena oil, cypress oil, lime pepper oil, magnolia oil, or any combination thereof.

55. The method according to any one of claims 42-53, wherein the one or more essential oil components comprise rosemary oil, ylang-ylang oil, cinnamon bark oil, cinnamon leaf oil, or any combination thereof.

56. The method according to any one of claims 42-55, wherein the one or more essential oil components comprise citral, methyl eugenol, 2-methoxycinnamaldehyde, trans-cinnamaldehyde, trans, trans-2,4-decanoic acid, benzaldehyde, 1,8-cineole, α-pinene, or any combination thereof.

57. The method according to any one of claims 42-56, wherein the first mixture further comprises a surfactant.

58. The method of claim 57, wherein the surfactant comprises a nonionic surfactant.

59. The method of claim 58, wherein the surfactant comprises polysorbate.

60. The method according to any one of claims 42-59, wherein the second phase comprises vesicles with an average diameter of about 100 nm to about 200 nm.

61. The method according to any one of claims 42 to 60, wherein the second phase comprises vesicles having a d90 diameter distribution of up to about 450 nm.

62. The method according to any one of claims 42-61, wherein one or more glycerol monoesters each independently comprises a compound of formula Ii or formulas I-ii: (Formula II) (Formula I-ii) in: R A1 and R A2 Each is independently selected from H and C1-C6 alkyl groups; and R H It is C3-C 27 Side chain.

63. The method of claim 62, wherein R A1 and R A2 Each is represented by H.

64. The method according to claim 62 or 63, wherein R H It is a saturated, unsubstituted side chain.

65. The method according to any one of claims 62-64, wherein R H It is C 11 –C 21 Side chain.

66. The method according to any one of claims 42-65, wherein the second mixture further comprises C4–C 28 One or more salts of fatty acids.

67. The method of claim 66, wherein each of the one or more salts independently comprises a compound of formula II: (Formula II) in: R H It is C3-C 27 Side chain; and X n+ It is a cation portion with a formal charge n.

68. The method of claim 67, wherein X n+ Selected from Li + Na + K + Cs + Ag + Ca 2+ Mg 2+ Zn 2+ Cu 2+ and (R) D )4N + ,and Each occurrence of R D Selected from H, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl, wherein Each C1-C6 alkyl group is optionally surrounded by 1-3 R groups. E Replace, R E Independently selected from C3-C6 cycloalkyl, C3-C6 heterocycloalkyl, aryl, and heteroaryl; and Optionally, one or more R D They combine with the nitrogen atoms to which they are attached to form C3-C6 heterocyclic alkyl groups.

69. The method according to claim 67 or 68, wherein R H It is a saturated, unsubstituted side chain.

70. An emulsion prepared by the method according to any one of claims 42-69.

71. A method for coating agricultural products, the method comprising: The surface of the agricultural product is brought into contact with the emulsion according to any one of claims 1-41 and 70; and At least a portion of the aqueous medium is removed to form a coating on the surface of the agricultural product.

72. A method of coating agricultural products, the method comprising contacting the surface of the agricultural product with a first emulsion and a second emulsion, wherein: The first emulsion comprises a first aqueous medium and a first phase dispersed in the first aqueous medium, the first phase comprising one or more essential oil components; and The second emulsion comprises a second aqueous medium and a second phase dispersed in the second aqueous medium, the second phase comprising C4–C 28 One or more monoglycerides of fatty acids.

73. The method of claim 72, wherein the method comprises: The surface of the agricultural product is brought into contact with the first emulsion and at least a portion of the first aqueous medium is removed to produce a treated surface of the agricultural product. and The treated surface is brought into contact with the second emulsion and at least a portion of the second aqueous medium is removed to form a coating on the treated surface of the agricultural product.

74. The method of claim 72, wherein the method comprises: This allows the surface of the agricultural product to come into contact with the first and second emulsions; and At least a portion of the first aqueous medium and at least a portion of the second aqueous medium are removed to form a coating on the surface of the agricultural product.

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